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000611055 245__ $$aBorylation and rearrangement reactions of azasilaanthracenes to afford B,N-doped nanographenes
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000611055 520__ $$aAn air-stable B3,N3-containing dibenzobisanthene (8) was prepared in 29% yield by heating a 1,3,5-tri(aza silaanthryl)benzene (5) with BBr3 (180 °C). Under these conditions, the reaction does not stop after three fold SiMe2/BBr exchange but proceeds further via two rearrangement and two intramolecular C–H borylation steps. Some mechanistic details were unveiled by using smaller model systems and applying lower reaction temperatures. According to X-ray crystallography, compound 8 has a helically distorted scaffold. Due to its multiple resonance structure, it shows a narrow-band blue-green emission (λem = 493 nm; ΦPL = 84%; FWHM = 0.20 eV; THF); samples measured in PMMA gave prompt and delayed fluorescence lifetimes of 10.7 ns and 136 µs, respectively. The optical properties of 8 and of structurally related species were also investigated by quantum-chemical means: most of these compounds exhibit a small energy gap ΔEST between the lowest excited singlet (S1) and triplet (T1) states and a non-negligible spin–orbit coupling (SOC) between S1 and T1/T2, demonstrating their potential as thermally activated delayed fluor escence (TADF) emitters
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000611055 7001_ $$0P:(DE-HGF)0$$aValverde, Danillo$$b1
000611055 7001_ $$0P:(DE-H253)PIP1110297$$aNeubaur, Robert$$b2
000611055 7001_ $$0P:(DE-HGF)0$$aKarger, Sebastian$$b3
000611055 7001_ $$0P:(DE-H253)PIP1026845$$aVirovets, Alexandr$$b4
000611055 7001_ $$0P:(DE-HGF)0$$aBolte, Michael$$b5
000611055 7001_ $$0P:(DE-HGF)0$$aLerner, Hans-Wolfram$$b6
000611055 7001_ $$0P:(DE-HGF)0$$aOlivier, Yoann$$b7$$eCorresponding author
000611055 7001_ $$0P:(DE-H253)PIP1102807$$aWagner, Matthias$$b8$$eCorresponding author
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